Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules

[img]PDF - Authorized users only
Language: English
164Kb
Title:Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules
Creators:
Alexandrová, Zuzana
Stará, Irena G.
Sehnal, Petr
Teplý, Filip
Starý, Ivo
Šaman, David
Fiedler, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 12, pp. 2193-2211
Uncontrolled Keywords:Synthesis design, Helical structures, Palladium, Chirality, Cross-coupling, Copper, Alkynes, Arenes

Abstract

We have developed the synthesis of model nonracemic aromatic triynes (-)-(<i>S</i>)-<strong>1</strong>-<strong>4</strong> containing&nbsp;the 1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((<i>S</i>)-1-methylprop-2-yn-1-yl)oxy]- methyl}naphthalene&nbsp;unit. The common 1,2-di(2-substituted-1-naphthyl)acetylene part was constructed via Sonogashira coupling of appropriate 1-iodonaphthalenes with 1-ethynylnaphthalenes both bearing tethered acetylene units in positions 2. The chirality of triynes (-)-(<i>S</i>)-<strong>1</strong>-<strong>4</strong> was introduced by incorporating commercially available (-)-(<i>S</i>)-but-3-yn-2-ol (<strong>10</strong>) into tethered acetylene units. The nonracemic triynes are intended to be used as substrates in stereoselective [2+2+2] triyne cycloisomerization catalyzed by transition metal complexes. <p>

Title:Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules
Creators:
Alexandrová, Zuzana
Stará, Irena G.
Sehnal, Petr
Teplý, Filip
Starý, Ivo
Šaman, David
Fiedler, Pavel
Uncontrolled Keywords:Synthesis design, Helical structures, Palladium, Chirality, Cross-coupling, Copper, Alkynes, Arenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:12
Page Range:pp. 2193-2211
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20042193UNSPECIFIED
ID Code:2330
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Alexandrová, Zuzana; Stará, Irena G.; Sehnal, Petr; Teplý, Filip; Starý, Ivo; Šaman, David; Fiedler, Pavel (2004) Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules. Collection of Czechoslovak Chemical Communications, 69 (12). pp. 2193-2211. ISSN 0010-0765

Repository Staff Only: item control page